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Upgrading Windows

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When considering an upgrade install, you need to ensure that the version of the operating system you’re starting with is able to be upgraded to Windows Server 2022. Table 3-1 tells you which operating systems you can upgrade from and which edition of Windows Server 2022 you can upgrade to.

As a general rule, you can update to the newest Windows Server operating system directly as long as you’re within the last two major releases.

TABLE 3-1 Windows Server 2022 Upgrade Compatibility Matrix

If you’re running this edition … You can upgrade to these editions …
Windows Server 2016 Standard Windows Server 2022 Standard or Datacenter
Windows Server 2016 Datacenter Windows Server 2022 Datacenter
Windows Server 2019 Standard Windows Server 2022 Standard or Datacenter
Windows Server 2019 Datacenter Windows Server 2022 Datacenter

You also need to check with your application vendors to ensure that the applications on the server are compatible with Windows Server 2022. If they aren’t, then you may need to upgrade your applications before you upgrade the server operating system.

There is no direct upgrade path from Windows Server operating systems that are older than Windows Server 2016. If you’re migrating from an older server, start with a clean installation. If you can’t use a clean installation, you’ll need to upgrade to either Windows Server 2016 or Windows Server 2019 to be able to upgrade to Windows Server 2022.

After you’ve verified that you’re on a compatible version, you can begin the upgrade install. For this example, I’ll start with a Windows Server 2019 Standard installation and upgrade it to Windows Server 2022 Standard. Follow these steps:

1 Log in as the administrator on the system that you want to upgrade.

2 Insert the disc or other installation media into the system that you’re wanting to upgrade, and run setup.exe.The next screen asks if you want to download updates and drivers ahead of time (see Figure 3-6).FIGURE 3-6: Choose to either keep your files and settings or start fresh.

3 On the Install Windows Server screen, click Next.Any relevant updates will be downloaded. You may be required to reboot before you're able to continue. On the Install Windows Server screen, you’ll see a Change How Setup Downloads Updates link. Clicking this link allows you to not patch the server at the time of installation. I don’t recommend doing this unless the server doesn’t have an Internet connection, because it will be potentially vulnerable to attack until it’s patched.

4 Select Windows Server 2022 Standard with Desktop Experience (or whichever version you want) and click Next.

5 Read through the license terms if you have time on your hands, and then click Accept.On the next screen, you choose whether to keep your personal files and apps or keep nothing. If you’re sticking with the same experience (Core or Desktop), you’ll see both options. If you’re changing the experience, the only option you’ll have will be to keep nothing.

6 If you have the option, select the Keep Personal Files and Apps radio button, and then click Next.If you want to start clean, you can select Nothing. Just be aware that you will lose data if you choose this option. In my case, because I’m using evaluation media, I can only choose Nothing. This screen is shown in Figure 3-6. If the Keep Files, Settings, and Apps option is grayed out, it may be because you’re trying to change the user experience (for example, from Core to Desktop), or you may be using evaluation media rather than retail media. In either case, you have to choose Nothing.The installer fetches any applicable updates and presents you with a summary screen.

7 If everything looks correct, click Install.The installer begins the upgrade install to Windows Server 2022. It may restart several times during this process.That’s it — you’re done!

Windows Server 2022 & Powershell All-in-One For Dummies

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